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generator question

if you are doing this for emergencies while you are not there use a automatic transfer switch, otherwise to connect it a manual one will do. Cost is vastly different here. a 15KW generator will be fine

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generator question

I have a vacation house with a sub well pump, and an oil fired furnace and the house is aprox 2,000 square feet.

What generator capacity in watts would be recommended to run the well pump, furnace, fridge, some lights and tv?

Is it an easy tie in from the generator to the control panel?

15KW is a bit over kill if your looking to just keep things running. You have and oil furnace and the only 220 that you will need to worrry about woulde be the well pump. Get a 10KW it will give you plenty of power to do what you want Well minus running the dryer or electric range

generator question

Geeze, 10kW? 15kW?????

For the bare minimum a 4000-4500 watt genny will do. To run more things at the same time, you can go up to 5000-6500 watts. Anything bigger is overkill and wasteful IMO. The quality of the unit is almost as important. I know folks who comfortably run bigger homes with 4500 watt Honda EX series gensets.
This is of course unless you want to go with an automatic standby unit. Then a 7kW is about the smallest you can go. They don't make standby unit much smaller.

Then again, you have a vacation home, money is obviously not much of an issue. Get the biggest one you can afford and run as much as you want.

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Answers based on the 2011 NEC.